Formation of the tetracyclo [5.4. 2.02, 6.02, 9] tridecane ring system by a novel transannular aldolization reaction

MN Deshpande, S Wehrli, M Jawdosiuk…

文献索引：Deshpande, M. N.; Wehrli, S.; Jawdosiuk, M.; Guy, J. T.; Bennett, D. W.; et al. Journal of Organic Chemistry, 1986 , vol. 51, # 13 p. 2436 - 2444

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被引用次数: 11

摘要

Attempts to employ the" aldol approachn5 to convert l-(1, 5-dioxopentyl)-cis-bicyclo [3.3. 0] octane-3, 7-dione (7) into the corresponding [5.5. 5.5] fenestrane derivative 8b were thwarted when the dialdehyde 7 underwent transannular cyclization instead to provide the two diastereomeric diketodiacetates 18a and 18b. The structures of the trans, trans isomer 1Sa and its cis, trans diastereomer 18b were assigned, on the basis of 1D and 2D NMR ( ...